Method of producing glycol esters of abietic acid



Patented Deer 29,1931 V v umTEDgsTA GEORGE M. Norman, OEWILMINGTON, hammer, Lemma rojrriaieoULEs-rownrm in COMPANY, or WILMINGTON, DELAWABEUA; GQBPORATION ,OE-DELAWAREQTQ 1 METHOD or PRODUCING No. Drawing.

My invention relates to t h e production of V glycol esters of abietic acid audit is theob ject of my invention to provide a method for r the production of glycol esters of abiet c acid.

In accordance with the method'embodying my invention, I effect the heating of a rosin,

V for example,

as is obtained 1 v distilled readily;

.gradefof gum rosin, or a'wood wood rosin, or gum rosin, such from pine wood,- a fossil resin, or other resin acid, as primaric acid, with a glycol. I mayuse a catalyst in order to facilitate the reaction; between the glycoland the rosin and upon completion ofthereaction V excess glycol and any low end of rosin wh chv carrying out vention to use a i has been'purified, as for example, by distilla- 7 catalyst there may my invention the glycol used tion. In carrying out the method embodying example, ethylene or other higher aliphatic glycols; and asa be used, for example, zinc dust, boric acid, 'or an operative'equivalent thereof.

of purified Wood rosin,for example, having an acid number 16-2, a melting point of 78 C. and grading H in color are heated with35 parts of ethylene glycol and5'parts of 'zinc dust. The heating should be. atabout 195 C. continuedfor about 12 hours with or 'without agitation.

hours at about 195. C. the temperature should be raised toabout 3009C. and; the pressure lowered to aboutIone-half inch of mercury inorder to distill 0a excess glycoland any low end of rosin which may be present. Aft er distillation off of excess glycol and any 7 rosin there will remain as residue-"about 270 parts of ester, having an acid number of fied by'the use of one part ofzinc dust and heating for about 16hours with the produc tion of an'ester havingan'acid number 16.

ESTEB r, ABIErIo AoIn Application filed August 10, tava' seiia no; 212,147.

therefore'it is desirable in maybe, for glycol, propylene glycol,

300 parts zincdust.

asasamenes oo ara a paaga 1f wood rosin, 35- parts of-ethylene glycolj an'd' oparts of boricacid may be heatedatabout- 195 9 for about 16' hours, with subsequent distillation off of excess glycol and-rosin at abOut B QOF CQurider a pressureof about one l haliinch offmercury. -There will be pro" 'duced about 290 partsof glycol ester, having an acid number 8 and a melting point of64 a 65.

7 The reaction produced by heating the rosin and ethylene glycol may be expressed by the following equation o G2HJOGOC19H2Q2+2H2OV he. propyle e glycol ester andrmgher aliphatic glycol esters may be prepared in a 7 similar manner.- The trimethylene. glycol ester may be made by heating g. of grade H rosin, 22 g. of trimethylene glycol and 0.6

g. zinc-dust to about 20090, for 15 hours. The temperature is then raisedtOaround 30L0 G. and the low end of rosin and excess trimethylene glycol removed by distilling un- 'trimethylene ,glycol'ester of abietic acid, hav

I ing an A. N. of 19, is recovered'as residue. As an example of the carry ng out of the method embodying my invention,

It will be. understoodithat the use of a catalyst is not essential, but as indicated faated by increase in heating temperature, but

it will be appreciated that, for example, when V th 1 te he ting for b 12 e y ene glycol having a boiling point of sure over atmospheric will be required. 1

7 Having now fully described my invention,

M 7'5 der reduced pressure; About'78 g. of the]. 3 f

understood that the reaction may be acceler-f whatfI claim and desire to protect by Let-v -ters'Patent is: 7 j I r The method of producing glycol esters ofabietic acid, Which includes'heating rosin with an aliphatic glycol in the presence of 2; The method ofabietic acid, which includes distilling rosin,

heating the distilled rosin with an aliphatic of producing glycol esters. I I

, 195 C. to form an ester and o 5. The method of producing 2i glyc'olestef of abietic acid, WhlCh'lIlCllldQS distillingirosin, r

glycol and zinc dust at a temperature of about distilling ofl' excess glycol at about300 C. under reduced pressure. I

3. The method of producing a glycol ester of abietic acid, which includes heating rosin with ethylene; glycol and zincdust. i

4'. The method of of abietic acid, which includes heating rosin with ethylene glycol and zinc dust and'distillingo'fl the excessethylene gl yicol under reduced pressure.

heating the distilled rosin withan alliphetie glycol and'zinc-dust at about 195 C. forabout six; hours and distilling ofi and low end of rosin at" about-300? C. under a pressure of about one-half inch of mercury.

Inftestimony of which invention,*I-have hereunto. set my hand at Wilmington, Dela-Y Ware, on this Qndday of August, 1927.

producing a glycol the excess glycol v GEORGE M. NORMAN. 

